A river winding through a forest with autumn foliage.

Ashland Vacation Rentals

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Check prices for these dates

In two weeks
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Ashland vacation rentals

Private kitchen

Charming 3-bedroom house in delightful Ashland for your getaway

Charming 3-bedroom house in delightful Ashland for your getaway
Ashland
10.0 out of 10, Exceptional, (2 reviews)
"This is our second stay here and both times have been good. The house is quiet, even for it being on a well traveled road. "
United States
John W.
$281 nightly
The price is $297
Jul 5 - Jul 6
Total with taxes and fees
Charming 3-bedroom house in delightful Ashland for your getaway
Premium Apartment | Living area | 24-inch Smart TV with digital channels

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.6 out of 10, Excellent, (33 reviews)
"Charming room, fresh towels, clean!! I would stay here again."
United States
Mary
$266 nightly
The price is $306
Jul 3 - Jul 4
Total with taxes and fees
The Chester Hotel
Living area

On River/Harvard Sq. two blocks

On River/Harvard Sq. two blocks
West Cambridge
8.0 out of 10, Very Good, (46 reviews)
"Very convenient for our stay with a grandson attending Harvard"
United States
Christy
$271 nightly
The price is $310
Jul 5 - Jul 6
Total with taxes and fees
On River/Harvard Sq. two blocks
Terrace/patio

Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,224 reviews)
"Excellent stay as always, my home away from home when traveling in the area."
United States
Sean
$170 nightly
The price is $190
Jul 5 - Jul 6
Total with taxes and fees
Crescent Suites Hotel
Suite (Luxury 1BR w/ King Bed & City Views) | Egyptian cotton sheets, premium bedding, down comforters

Symple Live

Symple Live
4.5 star property
Fenway–Kenmore
9.0 out of 10, Wonderful, (6 reviews)
"The property was great, aside from very busy outside streets, which made it difficult to sleep, but was not the fault of the host."
United States
Nicholas
$248 nightly
The price is $285
Jul 5 - Jul 6
Total with taxes and fees
Symple Live
Desk, iron/ironing board, WiFi, bed sheets

The Chester: Urban Chic Stay In South End

The Chester: Urban Chic Stay In South End
South End
10.0 out of 10, Exceptional, (1 review)
"We had a great stay in Boston and the Chester was perfect for our trip. First time in Boston so we did a lot of the usual things, but this location was great to easily connect with bus and train options as we decided not to rent a vehicle. Space was comfortable for group of three - lots of shops and restaurants in the area. We were touring a lot, so didn’t spend a lot of time in the unit, but it was very comfortable and would definitely come back again!"
United States
Chad T.
$300 nightly
The price is $345
Jul 5 - Jul 6
Total with taxes and fees
The Chester: Urban Chic Stay In South End
2 bedrooms, WiFi, bed sheets

Great Apartment on River/ Harvard Square two blocks

Great Apartment on River/ Harvard Square two blocks
West Cambridge
8.4 out of 10, Very Good, (37 reviews)
"Clean apartment. Close to Harvard Square. Stairs not user-friendly."
United States
Jeffrey
$275 nightly
The price is $315
Jul 6 - Jul 7
Total with taxes and fees
Great Apartment on River/ Harvard Square two blocks
Exterior

Stylish Back Bay Retreat, Steps from Prudential

Stylish Back Bay Retreat, Steps from Prudential
Back Bay
9.0 out of 10, Wonderful, (12 reviews)
"Excellent location for restaurants, shops, sightseeing. Lovely buzz around the area, with park & river close by to escape if necessary. Large lounge area to put your feet up between trips, and adequate glasses etc for drinks and nibbles between the treats at the bakeries and restaurants nearby."
United Kingdom
Jude
$337 nightly
The price is $362
Jul 14 - Jul 15
Total with taxes and fees
Stylish Back Bay Retreat, Steps from Prudential
Exterior

Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St
2.0 star property
Back Bay
8.2 out of 10, Very Good, (179 reviews)
"Room was clean and near the shops of Back Bay"
United States
Steven
$91 nightly
The price is $105
Jul 5 - Jul 6
Total with taxes and fees
Maverick Suites at 245 Newbury St
Studio | Iron/ironing board, free WiFi

The Concord Hotel

The Concord Hotel
2.0 star property
South End
8.0 out of 10, Very Good, (2 reviews)
"There was very little loud construction outside the window as well as in the building before 8:30 am. The place was cute and relatively clean. Owners gave us a discount for the noise"
United States
Sara
$262 nightly
The price is $301
Jul 7 - Jul 8
Total with taxes and fees
The Concord Hotel
Exterior detail

Large 3BR Pet-Friendly Apt w/Free Parking Near Red Line-Downtown Boston 82

Large 3BR Pet-Friendly Apt w/Free Parking Near Red Line-Downtown Boston 82
Dorchester
9.4 out of 10, Exceptional, (36 reviews)
"Host was so receptive. The apartment was meticulously clean and subway very close by. Parking included. Great restaurants nearby and for us it was a great location. "
United States
Melissa W.
$525 nightly
The price is $603
Jul 27 - Jul 28
Total with taxes and fees
Large 3BR Pet-Friendly Apt w/Free Parking Near Red Line-Downtown Boston 82
TV

Charming 1 Bedroom | Newbury Street

Charming 1 Bedroom | Newbury Street
Back Bay
$344 nightly
The price is $444
Jul 10 - Jul 11
Total with taxes and fees
Charming 1 Bedroom | Newbury Street
TV

Modern 3BR Boston Nest • Pet-Friendly • Franklin Park & Red Line 558-2

Modern 3BR Boston Nest • Pet-Friendly • Franklin Park & Red Line 558-2
Dorchester
10.0 out of 10, Exceptional, (19 reviews)
"Very nice property, parking is safe, owner give clear checkin and checkout instructions. Very good."
United States
Kevin
$377 nightly
The price is $434
Jul 5 - Jul 6
Total with taxes and fees
Modern 3BR Boston Nest • Pet-Friendly • Franklin Park & Red Line 558-2
Exterior

Charming 2-bedroom apartment with WiFi, AC in superb Canton

Charming 2-bedroom apartment with WiFi, AC in superb Canton
Canton
9.4 out of 10, Exceptional, (23 reviews)
"Beds were comfortable, location was convenient for our needs, thankful for the shoveling and clearing of snow in the morning! "
United States
Stephanie G.
$181 nightly
The price is $202
Jul 5 - Jul 6
Total with taxes and fees
Charming 2-bedroom apartment with WiFi, AC in superb Canton
2 bedrooms, iron/ironing board, WiFi

Cozy 2-bedroom apartment in charming Dedham - Legacy Mall with WiFi

Cozy 2-bedroom apartment in charming Dedham - Legacy Mall with WiFi
Dedham
9.2 out of 10, Wonderful, (11 reviews)
"Great property, comfortable, accurate listing, and super attentiveness and support from Long, the host. Overall, a great stay while visiting family in the area! Thank you, Long!"
United States
John M.
$240 nightly
The price is $268
Jul 10 - Jul 11
Total with taxes and fees
Cozy 2-bedroom apartment in charming Dedham - Legacy Mall with WiFi
Outdoor dining

Stunning South End/Back Bay Penthouse!

Stunning South End/Back Bay Penthouse!
South End
10.0 out of 10, Exceptional, (107 reviews)
"Great stay for several days of college touring!! Had everything we could possibly need. Hosts were very quick to respond to any questions or concerns! "
United States
Anonymous traveler
$1,868 nightly
The price is $2,147
Jul 4 - Jul 5
Total with taxes and fees
Stunning South End/Back Bay Penthouse!
Apartment (3 Bedrooms) | Interior

Boston Duplex w/ Foosball Table: 11 Mi to Downtown

Boston Duplex w/ Foosball Table: 11 Mi to Downtown
3.0 star property
Hyde Park
$457 nightly
The price is $525
Jul 17 - Jul 18
Total with taxes and fees
Boston Duplex w/ Foosball Table: 11 Mi to Downtown
42-inch TV with satellite channels

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (157 reviews)
"Great location!"
United States
Kevin
$113 nightly
The price is $130
Jul 5 - Jul 6
Total with taxes and fees
Maverick Suites at 400 Columbus Ave
Fridge, microwave, oven, stovetop

Brand-new Modern 4BR Boston Comfortable Apartment w/Parking Pet-Friendly - 80/2

Brand-new Modern 4BR Boston Comfortable Apartment w/Parking Pet-Friendly - 80/2
Dorchester
9.4 out of 10, Exceptional, (23 reviews)
"Great property. Easy referral and I would stay there again."
United States
Dominic T.
$560 nightly
The price is $644
Jul 6 - Jul 7
Total with taxes and fees
Brand-new Modern 4BR Boston Comfortable Apartment w/Parking Pet-Friendly - 80/2
Outdoor dining

🎖The Ashmont Apartment - Close to Subway & Downtown Boston🎖

🎖The Ashmont Apartment - Close to Subway & Downtown Boston🎖
Dorchester
9.8 out of 10, Exceptional, (117 reviews)
"Beautiful clean apt in a lovely house. Great communication with host Eddie. Able to store our luggage early. Near transit. We would highly recommend this place for a visit to Boston"
Canada
patricia
$410 nightly
The price is $471
Aug 2 - Aug 3
Total with taxes and fees
🎖The Ashmont Apartment - Close to Subway & Downtown Boston🎖
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Ashland Hotel Reviews

Four Points by Sheraton Boston Newton

Four Points by Sheraton Boston Newton

10/10 Excellent
"This is the second time I stayed here this year, after not staying here in many years. Both visits have been excellent. Great value for the money, good location, and a few local eateries within walking distance. The parking garage was convenient. Most of all, however, Nakia went above and beyond to make this stay excellent. She addressed two special requests which were very helpful."
Thomas 1-night trip
Posted 1 hour ago
Four Points by Sheraton Boston Newton

Find out more about Ashland

Everything you need to know about Ashland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Ashland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Ashland vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Ashland vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Ashland. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Ashland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $105 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Ashland rentals

At Expedia, we put the best Ashland vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Ashland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Ashland vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Ashland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Ashland?

Yes, you can find vacation rentals near top local attractions in Ashland, or you can go with a more secluded option if you're looking for relaxation. Ashland is known for its shopping and restaurants. Make sure you have time to check out the lake views while you're in the area.

What are some of the best vacation rentals that Ashland has to offer?

Charming 3-bedroom house in delightful Ashland for your getaway: Visitors give good reviews to this Ashland vacation home rental, which comes with laundry facilities so you can feel at home during your trip.

How many vacation rentals are there in Ashland?

Expedia has 3 vacation rentals for your stay in Ashland.

What can I see and do in Ashland?

While exploring the area, visit family-friendly sights like Apex Entertainment Center, or get outside and enjoy nature at Framingham Town Common. Other places in town to visit include Ashland State Park and Hopkinton State Park.

What are vacation rentals like in Ashland?

Vacation rentals are private properties you can reserve for a couple days or more in Ashland. Vacation rentals provide amenities like WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from public hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for a small group gathering.